Akiyama R, Lee HJ, Nakayasu M, Osakabe K, Osakabe Y, Umemoto
N, Saito K, Muranaka T, Sugimoto Y, Mizutani M (2019)
Characterization of steroid 5α-reductase involved in α-tomatine
biosynthesis in tomatoes. Plant Biotechnol 36: 253–263
Akiyama R, Nakayasu M, Umemoto N, Kato J, Kobayashi M,
Lee HJ, Sugimoto Y, Iijima Y, Saito K, Muranaka T, et al.
(2021a) Tomato E8 encodes a C-27 hydroxylase in metabolic
detoxification of α-tomatine during fruit ripening. Plant Cell
Physiol 62: 775–783
Akiyama R, Watanabe B, Kato J, Nakayasu M, Lee HJ, Umemoto N,
Muranaka T, Saito K, Sugimoto Y, Mizutani M (2022) Tandem
gene duplication of dioxygenases drives the structural diversity
of steroidal glycoalkaloids in the tomato clade. Plant Cell Physiol
63: 981–990
Akiyama R, Watanabe B, Nakayasu M, Lee HJ, Kato J, Umemoto
N, Muranaka T, Saito K, Sugimoto Y, Mizutani M (2021b) The
biosynthetic pathway of potato solanidanes diverged from that
of spirosolanes due to evolution of a dioxygenase. Nat Commun
12: 1300
Cárdenas PD, Sonawane PD, Heining U, Jozwiak A, Panda S,
Abebie B, Kazachkova Y, Pliner M, Unger T, Wolf D, et al. (2019)
Pathways to defense metabolites and evading fruit bitterness
in genus Solanum evolved through 2-oxoglutarate-dependent
dioxygenases. Nat Commun 10: 5169
Choe S, Dilkes BP, Gregory BD, Ross AS, Yuan H, Noguchi T,
Fujioka S, Takatsuto S, Tanaka A, Yoshida S, et al. (1999) The
Arabidopsis dwarf1 mutant is defective in the conversion of
24-methylenecholesterol to campesterol in brassinosteroid
biosynthesis. Plant Physiol 119: 897–908
Friedman M (2002) Tomato glycoalkaloids: Role in the plant and in
the diet. J Agric Food Chem 50: 5751–5780
Friedman M (2006) Potato glycoalkaloids and metabolites: Roles in
the plant and in the diet. J Agric Food Chem 54: 8655–8681
Harrison DM (1990) Steroidal alkaloids. Nat Prod Rep 7: 139–147
Helmut R (1998) Solanum steroid alkaloids: An update. Alkaloids:
Chem Biol Perspect 12: 103–185
Iijima Y, Fujiwara Y, Tokita T, Ikeda T, Nohara T, Aoki K, Shibata
D (2009) Involvement of ethylene in the accumulation of
esculeoside A during fruit ripening of tomato (Solanum
lycopersicum). J Agric Food Chem 57: 3247–3252
Iijima Y, Nakamura Y, Ogata Y, Tanaka K, Sakurai N, Suda K,
Suzuki T, Suzuki H, Okazaki K, Kitayama M, et al. (2008)
Metabolite annotations based on the integration of mass spectral
information. Plant J 54: 949–962
Iijima Y, Watanabe B, Sasaki R, Takenaka M, Ono H, Sakurai N,
Umemoto N, Suzuki H, Shibata D, Aoki K (2013) Steroidal
glycoalkaloid profiling and structures of glycoalkaloids in wild
tomato fruit. Phytochemistry 95: 145–157
Itkin M, Heinig U, Tzfadia O, Bhide AJ, Shinde B, Cardenas
PD, Bocobza SE, Unger T, Malitsky S, Finkers R, et al. (2013)
Biosynthesis of antinutritional alkaloids in solanaceous crops is
mediated by clustered genes. Science 341: 175–179
Kozukue N, Yoon KS, Byun GI, Misoo S, Levin CE, Friedman
M (2008) Distribution of glycoalkaloids in potato tubers of 59
accessions of two wild and five cultivated Solanum species. J
Agric Food Chem 56: 11920–11928
Lang Y, Kisaka H, Sugiyama R, Nomura K, Morita A, Watanabe T,
Tanaka Y, Yazawa S, Miwa T (2009) Functional loss of pAMT
results in biosynthesis of capsinoids, capsaicinoid analogs, in
Capsicum annuum cv. CH-19 Sweet. Plant J 59: 953–961
Copyright © 2023 Japanese Society for Plant Biotechnology
Lee HJ, Nakayasu M, Akiyama R, Kobayashi M, Miyachi H,
Sugimoto Y, Umemoto N, Saito K, Muranaka T, Mizutani M
(2019) Identification of a 3β-hydroxysteroid dehydrogenase/3ketosteroid reductase involved in α-tomatine biosynthesis in
tomato. Plant Cell Physiol 60: 1304–1315
Lincoln JE, Cordes S, Read E, Fischer RL (1987) Regulation of
gene expression by ethylene during Lycopersicon esculentum
(tomato) fruit development. Proc Natl Acad Sci USA 84:
2793–2797
Nakayasu M, Akiyama R, Kobayashi M, Lee HJ, Kawasaki T,
Watanabe B, Urakawa S, Kato J, Sugimoto Y, Iijima Y, et al.
(2020) Identification of α-tomatine 23-hydroxylase involved in
the detoxification of a bitter glycoalkaloid. Plant Cell Physiol 61:
21–28
Nakayasu M, Akiyama R, Lee HJ, Osakabe K, Osakabe Y, Watanabe
B, Sugimoto Y, Umemoto N, Saito K, Muranaka T, et al. (2018a)
Generation of α-solanine-free hairy roots of potato by CRISPR/
Cas9 mediated genome editing of the St16DOX gene. Plant
Physiol Biochem 131: 70–77
Nakayasu M, Ohno K, Takamatsu K, Aoki Y, Yamazaki S, Takase
H, Shoji T, Yazaki K, Sugiyama A (2021a) Tomato roots
secrete tomatine to modulate the bacterial assemblage of the
rhizosphere. Plant Physiol 186: 270–284
Nakayasu M, Shioya N, Shikata M, Thagun C, Abdelkareem A,
Okabe Y, Ariizumi T, Arimura G, Mizutani M, Ezura H, et al.
(2018b) JRE 4 is a master transcriptional regulator of defenserelated steroidal glycoalkaloids in tomato. Plant J 94: 975–990
Nakayasu M, Umemoto N, Akiyama R, Ohyama K, Lee HJ, Miyachi
H, Watanabe B, Muranaka T, Saito K, Sugimoto Y, et al. (2021b)
Characterization of C-26 aminotransferase, indispensable for
steroidal glycoalkaloid biosynthesis. Plant J 108: 81–92
Nakayasu M, Umemoto N, Ohyama K, Fujimoto Y, Lee HJ,
Watanabe B, Muranaka T, Saito K, Sugimoto Y, Mizutani M
(2017) A dioxygenase catalyzes steroid 16α-hydroxylation in
steroidal glycoalkaloid biosynthesis. Plant Physiol 175: 120–133
Noguchi T, Fujioka S, Takatsuto S, Sakurai A, Yoshida S, Li J, Chory
J (1999) Arabidopsis det2 is defective in the conversion of (24R)24-methylcholest-4-en-3-one to (24R)-24-methyl-5α-cholestan3-one in brassinosteroid biosynthesis. Plant Physiol 120: 833–840
Ohnishi T, Yokota T, Mizutani M (2009) Insights into the
function and evolution of P450s in plant steroid metabolism.
Phytochemistry 70: 1918–1929
Ohyama K, Okawa A, Moriuchi Y, Fujimoto Y (2013) Biosynthesis
of steroidal alkaloids in Solanaceae plants: Involvement of an
aldehyde intermediate during C-26 amination. Phytochemistry
89: 26–31
Petersen HW, Mølgaard P, Nyman U, Olsen CE (1993)
Chemotaxonomy of the tuber-bearing Solanum species,
subsection Potatoe (Solanaceae). Biochem Syst Ecol 21: 629–644
Sánchez-Mata MC, Yokoyama WE, Hong YJ, Prohens J (2010)
α-Solasonine and α-solamargine contents of gboma (Solanum
macrocarpon l.) and scarlet (Solanum aethiopicum l.) eggplants. J
Agric Food Chem 58: 5502–5508
Sawai S, Ohyama K, Yasumoto S, Seki H, Sakuma T, Yamamoto T,
Takebayashi Y, Kojima M, Sakakibara H, Aoki T, et al. (2014)
Sterol side chain reductase 2 is a key enzyme in the biosynthesis
of cholesterol, the common precursor of toxic steroidal
glycoalkaloids in potato. Plant Cell 26: 3763–3774
Shakya R, Navarre DA (2008) LC-MS analysis of solanidane
glycoalkaloid diversity among tubers of four wild potato species
and three cultivars (Solanum tuberosum). J Agric Food Chem 56:
6949–6958
Sonawane PD, Heinig U, Panda S, Gilboa NS, Yona M, Kumar
SP, Alkan N, Unger T, Bocobza S, Pliner M, et al. (2018) Shortchain dehydrogenase/reductase governs steroidal specialized
metabolites structural diversity and toxicity in the genus
Solanum. Proc Natl Acad Sci USA 115: E5419–E5428
Sonawane PD, Jozwiak A, Barbole R, Panda S, Abebie B,
Kazachkova Y, Gharat SA, Ramot O, Unger T, Wizler G, et al.
(2022) 2-oxoglutarate-dependent dioxygenases drive expansion
of steroidal alkaloid structural diversity in the genus Solanum.
New Phytol 234: 1394–1410
Sonawane PD, Pollier J, Panda S, Szymanski J, Massalha H, Yona
M, Unger T, Malitsky S, Arendt P, Pauwels L, et al. (2016) Plant
cholesterol biosynthetic pathway overlaps with phytosterol
metabolism. Nat Plants 3: 1–13
Umemoto N, Nakayasu M, Ohyama K, Yotsu-Yamashita M,
R. Akiyama et al. Mizutani M, Seki H, Saito K, Muranaka T (2016) Two
cytochrome P450 monooxygenases catalyze early hydroxylation
steps in the potato steroid glycoalkaloid biosynthetic pathway.
Plant Physiol 171: 2458–2467
Yasumoto S, Sawai S, Lee HJ, Mizutani M, Saito K, Umemoto N,
Muranaka T (2020) Targeted genome editing in tetraploid
potato through transient TALEN expression by Agrobacterium
infection. Plant Biotechnol 37: 205–211
Yasumoto S, Umemoto N, Lee HJ, Nakayasu M, Sawai S, Sakuma T,
Yamamoto T, Mizutani M, Saito K, Muranaka T (2019) Efficient
genome engineering using platinum TALEN in potato. Plant
Biotechnol 36: 167–173
Zhao DK, Zhao Y, Chen SY, Kennelly EJ (2021) Solanum steroidal
glycoalkaloids: Structural diversity, biological activities, and
biosynthesis. Nat Prod Rep 38: 1423–1444
Copyright © 2023 Japanese Society for Plant Biotechnology
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